Sodium Azide → 4-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine

HRID 407217

반응식

HRID 407217 반응식
Br[C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH:11]([F:13])[F:12].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C>[N:14]([C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH:11]([F:13])[F:12])=[N+:15]=[N-:16]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 866754024,6-Dibromo-2-chloro-3-(difluoromethoxy)pyridine

생성물 1

HCID 866754034-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine수율 48.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

4,6-Dibromo-2-chloro-3-(difluoromethoxy)pyridine (780 mg, 2.312 mmol) was dissolved in DMF (5 mL), and sodium azide (180 mg, 2.77 mmol) was added. The reaction mixture was heated at 65° C. for 2 h and the progress of the reaction was checked by liquid chromatography-mass spectrometry (LC-MS). The reaction appeared to be mostly complete. The product was partitioned between Et2O and H2O. The aqueous phase was then extracted twice more with Et2O. The organic extracts were combined, diluted with petroleum ether, washed twice with H2O, dried, and concentrated. The product was purified by column chromatography (SiO2, EtOAc/hexane gradient) to yield 4-azido-6-bromo-2-chloro-3-(difluoromethoxy)-pyridine (0.335 g, 48.4%): 1H NMR (300 MHz, CDCl3) δ 7.26 (s, 1H), 6.59 (t, J=73.6, 1H).

후처리

  1. customThe product was partitioned between Et2O and H2O
  2. extractionThe aqueous phase was then extracted twice more with Et2O
  3. additiondiluted with petroleum ether
  4. washwashed twice with H2O
  5. customdried
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography (SiO2, EtOAc/hexane gradient)

출처 및 근거

ORD 기록
ord-936a03b1ed174943acf86b9cf6c1e710
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754229B2

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